When Failure Becomes Design

The leadership team had presented a slick five-year plan, with manicured slides and rock solid logic. Yet, the energy in the room felt off.

So I asked one uncomfortable question: “Imagine it’s November 2030, and this strategy has failed so completely, that the Harvard Business Review wants to turn this into a front page article on how NOT to do strategy. What happened?”

After a short silence, the flood gates opened: Too many priorities, untested assumptions and an organization drowning in daily business. In less than 20 minutes, they wrote the perfect movie script for their own failure.

That’s when I told them about the lamppost. When you ride a motorcycle, the instructor gives one rule: Don’t look at the lamppost. Because if you do, you’ll hit it: Your bike follows your eyes.

Strategy works the same way: If you obsess over failure, you’ll build for fear. However, if you study failure to understand it, you’ll build for strength.

Whenever I conduct a Pre-Mortem exercise, it isn’t about predicting disaster. It’s about engineering a system that makes failure impossible (which happens to be my favorite definition of strategic success).

One team member wrote, “We still have 28 priorities….” We killed 22 that afternoon. By 16:12, the strategy was no longer a bloated deck, but a streamlined system that kept their eyes on the road.

Boardroom Drill: The 20-Minute Pre-Mortem (Monday 9:00–9:20)

1. Open a single slide titled: “Our strategy failed completely. What happened?”
2. Give everyone three minutes to write their answers in silence.
3. Share insights round-robin, no discussion.
4. Cluster patterns into 5–7 root causes.
5. For each cause, create one design rule that makes it impossible.
6. Add the rules to page one of your strategy deck.
7. Delete every initiative that breaks any rule.

Do this once and your strategy stops being a plan. It becomes a system that never stares at the lamppost, only at the road ahead.